"I was seeing so many people who weren't willing to get arrested," the 27-year-old says. "I wanted to show them that even if you have something to lose, isn't this worth losing it for?"
Although he has become conditioned against trusting the police, Shepard's greatest lesson from Occupy Denver so far is a surprising one: "All of this has served to reinforce my never-ending optimism, in ways I never expected," Shepard says. "The only thing that is frustrating is the speed at which things are changing."
That increased speed level has begun to slow down again. Without tents for the medical station, the security group or any front desk, the number of responsibilities that used to fill the volunteers' days has decreased. While hecklers used to shout "Get a job!" out the window during trips down Broadway, they now yell "Go home already!"
"I feel like the camping area is my home and the kitchen is all of our home," says Shepard, sitting about three feet from the latter. "And I was willing to fight for them."
While we speak, Shepard is sharing a cigarette and looking directly into the sun. Last night, however, he slept in solar blankets during a freeze warning. "There's a lot less organized responsibility since we lost all of our tents. Now it's just 'Be out here.'"
Shepard, who grew up in Olney, Maryland, took a rather strange trip to Colorado. After a party ended and his friend Matt's dad kicked out everyone in his rental property, he decided to move to the state he had for a long time hoped to visit. "We left that day with just enough money to get out here," he says. "I've been to Boulder and Longmont and Denver, but I've yet to leave" over the course of two years -- about three months of it spent in Denver.
Thanks to a job at a barbershop and a landlord in Longmont who adjusted the friends' rent plan, the guys eventually progressed to the level of moderate rental bliss: Matt purchased an Xbox to go with his flat-screen, and Shepard paired his own with a PS3. That lasted until Shepard rented a hotel room for some homeless friends, a situation that, in a complicated string of events, landed him with drug charges, two months in jail and an eventual two years of probation. Newly released from jail, he joined the occupation twelve days ago.
"When I was arrested again when they were tearing down the Thunderdome, I fully expected to stay in jail," Shepard says. "I'm apprehensively grateful that there are so many people here who support me and believe in the movement, because this is definitely something worth fighting for. We need such a huge overhaul of the system."
But how does one overhaul it? Shepard's answer betrays the eloquence of a night spent in desperate cold and a morning that began early.
"The best way to describe it is 'Burn the motherfucker down.'"
More from our Occupy Denver archive: "Occupy Denver has a day of peace -- for now (PHOTOS)."